What the Cubs' Latest Signing Might Tell Us About Their Trade Deadline Plans

The Chicago Cubs made a quiet move on Tuesday, but it could have some loud implications.

Greg Jones signed with the franchise on a minor league deal. The 28-year-old outfielder was previously with the Milwaukee Brewers, appearing in 12 games this season for the big league squad. He spent the majority of his time in Triple-A, where he slashed .289/.423/.380 with an .803 OPS.

Milwaukee designated Jones for assignment back on July 12. He then decided to hit free agency, choosing to sign with their top NL Central competitor. All things considered, it now gives the Cubs a pretty good brain to pick when it comes to Brewers baseball, let alone somebody who has put together one of his better seasons as a pro.

A former first-round pick in 2019, it's clear that Jones has struggled to carve out a niche at the MLB level. One big reason for this has been his inconsistency at the plate, where he's struck out a lot and has seen his power come and go. With that said, he's clearly found a better rhythm in 2026, and he deserves credit for still drawing walks at a pretty solid rate. His OPS has remained respectable throughout his minor league career because of this.

There is also no denying his serviceability as a defender and speedster. At the end of the day, this is why he has gotten a taste of the majors in the past. He's stolen 21 bags in Triple-A this year and was once graded as having a 70 run value.

At the same time, don't the Cubs already have a player that fits a version of this description on the roster? They added Justin Dean to the major league roster only a handful of weeks back as their utility guy and base-runner. He's been decent in that role, albeit in limited action.

It's true that it doesn't hurt to have a few of these guys in the system, and it's worth mentioning that Jones has more MLB experience. Jones might also merely be another body for the Iowa squad, which could always use some veteran help and versatility. However, it's hard not to think about the looming trade deadline whenever a move is made at this time of year. And the addition of Jones, in particular, feels like it could signal the Cubs' willingness to move off a familiar face.

Are the Cubs Ready to Trade Kevin Alcantara?

Feb 28, 2026; Phoenix, Arizona, USA; Chicago Cubs designated hitter Kevin Alcantara (13) prepared for his at bat in the first inning of a spring training game against the Los Angeles Dodgers at Camelback Ranch-Glendale. Mandatory Credit: Allan Henry-Imagn Images | IMAGN IMAGES via Reuters Connect

All-in on a postseason pursuit and trying to catch the Milwaukee Brewers, the Chicago Cubs are expected to be among the most active teams at this trade deadline. Most anticipate at least one big move made for a starting pitcher, of which there should be many on the open market.

There have been a handful of Cubs prospects thrown around as possible trade bait, but arguably none have felt more likely to be on the move than Kevin Alcantara. The 24-year-old has been one of the Cubs' most talked-about youngsters for years. He is a massive outfielder with great speed and a big-time swing. May once thought that he would be part of the Cubs' day-to-day plans by now, but Alcantara is still waiting for the right opportunity.

Indeed, Alcantara's brief time in the majors has left something to be desired. His strikeout rate has been frustratingly high, as he just doesn't look as comfortable facing big league arms. Meanwhile, in the minors, he's looked as good as ever. Alcantara has an OPS of .936 with 17 homers and 42 RBIs in 55 games. It's not hard to see why Chicago has continued to give him chances, but it's also not hard to see why another team might be interested in giving him a longer MLB leash.

In other words, the Cubs need to be prepared to part ways with Alcantara in the coming weeks to fill their other roster holes. By signing a player like Greg Jones, they are essentially doing just that. He gives them another option to potentially call up if another injury arises. Of course, Alcantara is currently on the roster because of Matt Shaw's IL stint.

Heck, who is to say Matt Shaw doesn't come up in trade talks as the deadline nears? While this feels way less likely than moving Alcantara, there is no question that Shaw would help the Cubs lock in an even bigger move.

The whole point is that every decision has to be put under a microscope at a time like this. Is it possible this signing means nothing for Alcantara's future? Absolutely, but it's also possible that the Cubs are preparing for a world where they do need some additional outfield depth after the trade deadline. It could be the cost of doing business.

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